


A Very Supernatural Holiday Season

by timeladyofletters



Category: Supernatural
Genre: Angst, Christmas Drabbles, Christmas Fluff, F/F, F/M, Fluff, Fluffy, Gen, M/M, Multi, Reader-Insert, Reader-Interactive, christmas imagines, holiday drabbles, holiday imagines, multiple stories, romantic
Language: English
Status: In-Progress
Published: 2015-11-25
Updated: 2015-12-28
Packaged: 2018-05-03 06:19:40
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 18
Words: 7,529
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5280011
Author URL: https://archiveofourown.org/users/timeladyofletters/pseuds/timeladyofletters
Summary: <blockquote class="userstuff">
              <p>This is going to be a collection of SHORT Christmas/winter/holiday themed drabbles. Every chapter will be a new little story, and if all goes well, I'll be adding new ones from December 1st leading up to January 1st. They'll be an assortment of fluffy, romantic, sad, angsty, platonic, and whatever else.</p>
            </blockquote>





	1. Imagine Dean hanging mistletoe all over the bunker just to have extra excuses to kiss you

**Summary for the Chapter:**

> Reader x Dean - Fluff.

“Y/N, stop right there!” Dean practically shouted from his seat at the table. Before you could even ask why, he was up and heading in your direction; a sly smirk on his face and his finger pointing to something above you.

You looked up, and spotted yet another bundle of mistletoe handing over your head.

“Wha-  _again_?” you exclaimed. “That’s like the tenth time today!”

From the moment you awoke that morning, you had been finding mistletoe strung up to the ceiling in multiple places around the bunker; strategically placed in areas where you would surely be at one point or another. Dean had made sure to hang it in front of your bathroom mirror, over your seat at the table, and he was even able to somehow hang it over your side of the bed while you were asleep. 

And he never missed an opportunity to catch you standing under the leaves; though if you were being honest with yourself, you were hanging around the decorated areas on purpose. The extra kisses from Dean were definitely something you could get on board with.

Dean stood before you and waggled his brows suggestively. “Well you know me, babe, I’m all about the holiday traditions. Pucker up.”

You let out a fake scoff and rolled your eyes before grabbing Dean by the collar of his shirt and pulling his lips down to yours. His kiss tasted of coffee and sweet peppermint, as if he’d eaten a candy cane since you last kissed him half-an-hour earlier.

When you pulled away, Dean let out a happy sigh; his face the epitome of bliss. You, however, had to stifle your laughter when you noticed Sam browsing through the library. He was standing in front of the shelf that housed your favorite book, and just above him was yet another bundle of mistletoe.

“Hmmm, looks like someone else is in need of some winter lovin’,” you motioned towards the younger Winchester, who was totally oblivious to the abundance of greenery in the room.

The smile on Dean’s face vanished immediately and was replaced by a child-like frown. “Okay, this tradition just got old.”


	2. Imagine Sam getting glitter-bombed by your Christmas ornaments

**Summary for the Chapter:**

> Reader x Sam - Fluff

The lights you strung on your Christmas tree lit up the entire room when you plugged them in for the first time, and magic hung in the air. You and the boys had finally managed to be home at the bunker for Christmas, and after hours of decorating, it was almost perfect.  _Just a few more touches,_ you thought to yourself as your gaze swept over the mostly bare tree before you.

As if on cue, you heard familiar footsteps padding down the hallway in your direction.

"Well it’s about time,” you said, eyes never leaving the tree. “What took you so long?”

You turned around to see Sam walk into the room, struggling ever so slightly under the weight of your obscenely large box of tree ornaments. Without answering your question, Sam placed the box on the ground at your feet, and stood to his full height; a grim expression was plastered to his face, and it wasn’t hard to see why.

Sam was covered in glitter. Tonnes and tonnes of glitter. Greens, reds, golds, and every other color on the spectrum dotted him from the top of this head to the tips of his shoes. 

You clapped a hand to your mouth to stifle your laughter, but it was in vain. “Did you…did you get lost at a Mardi Gras party?” you teased.

“Your box of tree ornaments fell on me while I was trying to get it from the top shelf,” Sam explained. With every little movement he made, more and more glitter fell to the floor.

You couldn’t hold it in any longer, and you burst out laughing; doubling over and clutching your arms around yourself at the sight of the tough, sparkly hunter. “I’m sorry, but you look like-,”

“I look like a  _Twilight_ vampire!” Sam groaned, holding his arms out and lowering his head in defeat.

“Wait,” you stopped laughing as a sly look crept across your face. “How do you know what a  _Twilight_ vampire looks like?”

Sam’s eyes grew wide and a blush colored his cheeks. “I’m gonna take a shower,” he mumbled quickly as you resumed your giggles.

He was almost out of the room when you yelled teasingly after him, “Have a nice bath, Sammy Sparkles!”

Sam paused at the doorway, spun around, and rushed at you. In a flash, his arms were around you, pulling you into a bear hug as he shook his shaggy hair right above your head. Glitter poured down on you, the tiny flecks sticking themselves to every inch of your skin and the fabric of your clothes. When he finally let you go and took a few steps back, his previously sour expression had morphed into a blinding grin, and there was no way you could even pretend to be pissed.

“Looks like we  _both_ need a shower now, Y/N,” Sam smirked before he took your hand and led you out of the room; the both of you smiling and sparkling in the light of the Christmas tree.


	3. Imagine making snow angels with Castiel

**Summary for the Chapter:**

> Reader x Cas - Fluff.

“Cas! It’s too cold out here, let’s go back inside!” you shouted from the open doorway of your motel room; the breath from your words visible in the cold winter air.

What wasn’t visible, though, was Castiel.

With a groan, you bundled yourself in your thick coat and headed out in search of the angel. It wasn’t long before you found him in the field on the other side of the parking lot, laying on his back with his arms and legs spread out.

You would have been alarmed if it weren’t for the way he was moving his limbs back and forth in the snow.

“Uh, what are you doing?” you asked him.

Cas opened his eyes at the sound of your voice and stared up at you with those intense baby blues. “I’m making a snow angel.”

“An angel making snow angels? Kind of redundant, don’t you think?” you teased lightly.

“Perhaps,” Cas replied with a smile before pausing his movements to ask, “Would you like to join me, Y/N?”

If anyone else had asked, you would have answered with a stern ‘hell no’, because it was just too damn cold to be laying down in the snow; but there was no way you could ever turn Cas down. 

Instead, you took a seat on the ground beside him and laid on your back. “Sure,” you told Cas. “We can make our own snow angel garrison.”

“Our own garrison?” echoed Cas. “I’d like that very much.”

Without another word, you and Cas proceeded to wave your arms and legs through the snow; both of you allowing your hands to “accidentally” brush against each other with every movement. And ever though the snow had seeped through your clothes, Cas’ little touches were somehow able to keep you warm.


	4. Imagine Dean keeping you warm after you almost freeze to death

**Summary for the Chapter:**

> Reader x Dean - Angst.

Dean squeezed his eyes shut as he held you close to his chest.

_I was so reckless_ , he thought to himself.  _So stupid._

In typical Dean Winchester fashion, he was blaming himself. He was the one who had the brilliant idea of going out in the snowy field behind the rundown house you were staying in. He was the one who started the snowball fight. And it was his fault that you nearly became a Y/N-cicle.

It all happened so quickly; you and Dean were running around, laughing hysterically as you pelted snowballs at each other. After a while, Dean stopped to catch his breath as you continued to run. He couldn’t take his eyes off of you, it had been so long since he’d seen you so happy and free. Your laugh was infectious and you glowed of joy from the inside out. Dean considered it a privilege to even be in your presence.

Then he blinked, and you were gone.

It had taken him three seconds too long to realize that you had fallen into an icy pond, covered under a blanket of snow. By the time he dove in after you and pulled you out, your lips had turned blue and you were unconscious, but you were still breathing. And it was those tiny movements, the minuscule rise and fall of your chest, that Dean focused on as he wrapped you in blankets and held onto you for dear life.

“I’m so sorry, Y/N,” Dean murmured against your wet hair. “I should have stopped it before it happened. I should have been faster.”

If you were awake, you would have told him to break up the pity party and go easy on himself. It was no one’s fault. But you weren’t awake. Instead, you lay limp in his arms in as you thawed in front of a crackling fire. 

Dean spent the next few hours talking to you, telling you stories of his childhood and verbally reliving his favorite memories of you. He spoke as if you could hear him, and maybe you did, because the sound of his voice prompted you to let out a small sigh in your sleep and snuggle further into Dean’s embrace.

Your movements were sure signs of life, and Dean smiled down at your now peaceful face.

“You’re gonna be okay,” Dean promised quietly. Then he pressed his lips to your forehead and rocked you back and forth, hoping that the blankets, the fire, and his body were enough to keep you warm for the night.


	5. Imagine you and Sam celebrating your baby's first Christmas

**Summary for the Chapter:**

> Reader x Sam - Fluff.

“See Y/N? I told you she’d look adorable in it!” Sam exclaimed as he took baby Celeste into his arms, who was dressed in a tiny Santa Claus outfit, complete with the iconic red and white hat.

“Yeah, yeah,” you rolled your eyes. “Well to be fair, she’d look adorable in anything.”

Dean flocked to your side as well, and it was an amazing sight to see the two men cooing down at the baby. 

“Looks like Uncle Dean has good taste,” Dean smirked, praising himself for selecting the outfit in the store. It was Sam’s turn to roll his eyes, this time at his older brother. 

“Looks like Uncle Dean better be getting the rest of us some pretty awesome presents then, seeing as how he has such good taste,” Sam teased; all while looking down at Celeste and using his baby voice, which was pretty similar to his actual voice but slightly higher.

Dean mumbled something under his breath before heading back into the kitchen, and Sam went back to cuddling the baby. You had to take a moment to just stop and watch them together, and your heart filled with joy at the sight of your little family. It was amazing how someone as large and strong as Sam could be so sweet and gentle, yet there he was, carrying the tiny baby around the room safely in his arms as if she were the most precious thing in the world.

When he came back to you, Sam was holding something else in his hands along with Celeste - a small jewelry box.

“I know it’s a few days early,” he explained, “but Celeste and I couldn’t wait to give this to you.”

You took the velvet box and quirked a brow up at him. “Well I know it’s not a ring because I’ve already got one of those,” you said as your gaze flickered between the matching wedding bands you and Sam had exchanged two years earlier.

“Just open it,” Sam urged, his eyes bright with excitement.

So you did what he said, and found a beautiful silver locket nestled in the box. “Sam,” you gasped, “its…”

“Open that, too,” Sam cut you off, nodding towards the piece of jewelry. 

You opened the locket to reveal a small picture of you holding Celeste, with Sam’s arms around the both of you. You remembered the day the picture was taken well; it was when Celeste was born, seven months ago.

And now you could carry your family around with you, always.

“It’s perfect,” you told him as you clasped the chain around your neck.

“Merry Christmas, Y/N,” Sam murmured, leaning down to kiss you while your smiling daughter was happily trapped between the two of you.


	6. Imagine making Team Free Will wear ugly Christmas sweaters

**Summary for the Chapter:**

> Reader x TFW - Fluff. Inspired by this gif: http://45.media.tumblr.com/ae50ffa773c4cbbfdb48fa5541f99886/tumblr_nrtmaxlXe11qc2fi0o8_500.gif

“Wow, you guys make those ugly sweaters look…less ugly,” you noted in surprise as you focused the camera on Sam, Dean, and Cas.

“We know,” shrugged Cas, who had insisted on wearing his signature trench coat over his sweater.

Dean kept fidgeting with his clothes; tugging on the scratchy material and making annoyed faces in your direction. “I can’t believe you talked us into wearing this crap, Y/N,” he grumbled.

“Yeah well, at least I’m not the one who gave them to you in the first place, that was all Charlie. Now can you please fake a smile so we can film this video message for her?” you asked as nicely as you possibly could.

Dean shot you a blank look.

“Come on Dean,” Sam chimed in as the voice of reason. “The faster we do this, the faster we can change and burn these sweaters in a fire.”

“Fine. But you guys owe me so many Christmas cookies that it’ll make me sick.”

Cas tilted his head in confusion. “I don’t understand, is that a good thing?”

“Guys!” you said loudly, calling their attention back to you. “Lets just do this, okay? I’m hitting record in 3…2…1…”

In unison, the three men placed their hands on their hips and began to speak.

“Heya Charlie,” greeted Dean. “Thanks for the sweaters.” His gratitude was so fake, but you appreciated the effort.

“Merry Christmas!” Sam said, obviously trying to keep himself from laughing.

Then Cas smiled at the camera and concluded with, “We miss you, and we’ll see you soon.”

You stopped the recording and let out a sigh of relief.  _Well,_  you thought to yourself,  _that went better than I thought it would._


	7. Imagine Cas taking care of you when you get drunk at a holiday party

**Summary for the Chapter:**

> Reader x Cas - Fluff.

“You bitch!” you cursed loudly at the coffee table you had stumbled into, causing you to spill your spiked eggnog on your red shirt. You reeled your leg back to kick at the damn thing when Cas grabbed your shoulders and tugged you back.

“Don’t fight the table Y/N,” he said, trying to be as patient as possible. “It can’t fight back.”

“You’re so smart, Cas,” you slurred. “I’m gonna clean up.”

You stood in place for a few seconds, waiting for the room to stop spinning, before you trudged towards the bathroom to get cleaned up; brazenly pushing through groups of people on the way.

“Someone just tell me she’s going to be okay,” Cas sighed to Sam and Dean, who were also trying to keep a wary eye on you.

“Yeah Cas, she’ll be fine. Just be sure to stay with her all night,” answered Sam.

“And no more booze for her either. Y/N is on an all water diet until she’s sober,” Dean said as Cas followed behind you. He had almost caught up to you when some random guy, who looked more wasted than you did, beat you to it.

“Hey hot stuff, can I get you a drink?” the man proposed, his beer breath fanning your face.

“No, thanks,” you replied. You took a wobbly step back and shook your head. You were drunk, not stupid, and there was no way that you were going to accept a drink from a stranger.

“Come on, I can show you a good time!” he insisted, winding an unwelcome arm around your waist and pulling you towards him.

You were about to panic and scream bloody murder in order to get the creep away from you, but before you could, he was thrown to the ground at your feet. When you looked up, Cas was standing before you, giving the guy the death stare.

“She said no,” growled the angel. As soon as his eyes landed on you, his whole demeanor softened. “Are you alright, Y/N?” Cas asked as he wrapped an arm around your shoulders.

“I am now,” you murmured, leaning into him. “I just wanna go home and sleep. Or puke.”

Cas let out a small laugh and began to lead you out the door. “It’s okay, you can do both.”


	8. Imagine surprising Dean with yourself as his present while he's away on a hunt

**Summary for the Chapter:**

> Reader x Dean - Fluff (and nsfw if you squint really hard).

**Notes for the Chapter:**

> For a visual of what Y/N is wearing, open this link (not explicit, don't worry) - https://49.media.tumblr.com/55bb60a38f7d99cbaa816716935d26e3/tumblr_ns9y8i6kpN1tltwqqo8_250.gif

You took great pleasure in the way Dean’s jaw practically dropped to the floor when you removed your coat and dropped it to the floor.

“Merry Christmas, Dean,” you said to him.  


And it was going to be a merry one indeed. When Dean called you the day before to tell you that the hunt he was on was taking longer than expected and he wouldn’t be able to make it home for the 25th, you decided to take matters into your own hands. So you warned Sam to get his own motel room for the night, got an outfit ready, and made the 9 hour drive to your boyfriend.

You were nervous at first, because the “clothes” you had chosen for the occasion were much more brazen than anything you had ever tried before. You would have been extremely self conscious if it weren’t for the way that Dean was looking at you - his eyes slowly taking you in from top to bottom, briefly pausing on the large red ribbon you had tied in a bow around your chest and then trailing down to your matching red panties and stockings.

Dean’s gaze made you feel sexy and beautiful, because dammit, you really were.

“Wow, you’re just…wow,” Dean uttered in shock.  


“Thanks?” you said, more like a question than a statement.  


“No, seriously Y/N, just you being here is the best present you could give me, but seeing you like this? I have no words right now,” he explained as he took a few steps towards you.  


You couldn’t help the blush that crept to your cheeks at his words. When he was standing just in front of you, Dean wound one arm around your waist, and used his other hand to toy with the ends of the bow.

“So, uhh,” he hesitated. “Can I open my present now?” he asked, quirking a brow and grinning suggestively.  


“I don’t know,” you replied. “It isn’t Christmas for another two hours, maybe I should make you wait.”

“You wouldn’t,” Dean said in slight shock, right before you pushed up onto your toes and kissed him, nipping his bottom lip with your teeth in the way that you knew drove him wild.  


Then you pulled back and said breathlessly, “You’re right, I wouldn’t.”

Without another word, Dean’s fingers grasped the very edge of the bow, and slowly began to pull it open; his eyes never leaving yours as he did so.

**Notes for the Chapter:**

> **Note - I know that having a gif of someone else as ‘Y/N’ kinda ruins the whole reader insert experience, but it was too perfect to pass up. Also, Brooke Davis is flawless**


	9. Imagine Sam showing up at your door on Christmas Eve while Dean is in Purgatory

**Summary for the Chapter:**

> Reader x Sam - Angst.

“Sam, come inside. You’re going to get sick,” you urged a weary Sam, who had been rambling incoherently from the moment you opened your door to see him standing outside your motel room while the snow flurried around him.

Your pleading somehow got through to him, and he gave you a small nod before shuffling inside your house. You then sat him on the couch and excused yourself to get him something warm to drink when he grabbed your wrist and tugged you back down beside him.

“Don’t leave,” he begged, his voice small and frail. “Please.”

“Talk to me, Sam,” you told him. “Tell me what’s wrong.”

Sam huffed a deep breath and let it out slowly before speaking again. “I shouldn’t be here, Y/N. I should be wherever Dean is, and Dean should be the one who’s safe and alive; not me.”

“Don’t say that,” you said, placing your hand over his own. “We’ve been down this road before. We’ve tried to find Dean, but we keep coming up empty. I’m so sorry Sam, but you can’t keep blaming yourself.”

Sam shook his head back and forth and squeezed his eyes shut. “How could I not? Here I am, sitting with you on Christmas Eve. Meanwhile, Dean could be back in Hell for all we know. Or worse.”

It broke your heart, seeing Sam like that. You had rarely seen him in such a vulnerable state, but since his brother suddenly went missing, Sam had been different. “You cant give up, Sam. Not on him and certainly not on yourself. We’ll find answers. Maybe not right now, but someday. I promise you.”

“And what do we do until then?”

You could feel the pain and confusion radiating from the man sitting beside you, and you wished more than anything that you could fix it all for him, if only for just one night. But there was no magical solution to this, not this time. So instead, you wrapped your arms around him, pulling him into a warm embrace. He relaxed into you almost instantly, and tucked his face into the crook of your neck.

“We have to have hope,” you murmured soothingly as you ran your fingers through his hair, still damp from the snow. “I mean, that’s what the holidays are all about, right? Hope and miracles and all that. I know it’s not much but…”

“…its enough,” Sam cut in. Then he wound his arms around your waist, reciprocating both the hug and the comfort that you were providing him. “For now Y/N, its enough.”


	10. Imagine volunteering at a soup kitchen with Cas

**Summary for the Chapter:**

> Reader x Cas - Fluff.

“I gotta say Cas, when you suggested that we go out for lunch, this is the last place I expected you’d bring me to,” you told the angel standing beside you.

Cas’ smile faltered a bit and his blue eyes met yours. “I’m sorry, Y/N. I know this is…unconventional…”

“No, not at all!” you said said suddenly, sloshing the tiniest amount of hot soup onto your shoes. “I’m glad you brought me here.”

And you were glad.You and Cas were at a local soup kitchen, volunteering to cook and serve and clean for those who didn’t have the resources to do it on their own. The place was packed with people of all ages and races, all with different circumstances and different reasons for being there; yet every last one of them smiled and treated you with kindness.

It was a wonderful thing to experience over the holidays.

“It makes me sad to see what some people have to struggle through,” you continued, “but it’s also amazing to see how they band together and persevere. I’ve seen some of the best examples humanity has to offer just in these two hours alone.”

“I knew you’d see it that way,” said Cas, with softest of smiles on his lips as he ladled a hearty helping of broth into an old man’s bowl. “I thought I understood your race after all my years of existence, but it wasn’t until I spent time among you all that I truly realized how miraculous my father’s creation is. My brothers and sisters could learn a lot from you all when it comes to strength and bravery.”

You pondered on his words for a moment, never yourself believing the human race to be anything close to what he was describing. That day though, being there with all of those people; that may be enough to change your perspective. You were snapped out of your thoughts when a loud crash sounded through the room. A young woman had tripped and dropped her tray, spilling soup all over her sweater.

Before you could make a move, the people nearest to the scene all deserted their seats to aid the woman and clean up the mess. A pregnant girl brought her a handful of napkins to help her dry off. Then a boy, who couldn’t have been older than twelve years old, removed his over-sized jacket and offered it to the woman to wear in place of her own soiled sweater. Many words of gratitude were exchanged, and by the time the dishes were off the floor, Cas was taking a fresh bowl of soup to the woman, along with a tray of bread for everyone to pass around and share.

After checking the woman over to make sure she was okay, Cas came back to stand beside you. “Earth can be a hard place,” he explained, “but these humans, they can get better. They’re just doing the best they can.”

His observation made you smile. “So are you, Cas,” you said, gently squeezing his hand with your own. “So are you.”


	11. Imagine you and Sam getting a picture taken with Santa Claus

**Summary for the Chapter:**

> Reader x Sam - Fluff.

Cheery holiday music, mixed with incessant chatter, wafted through the mall as you and Sam waited in line; surrounded by parents and screaming children.

“Come on Y/N, it’ll be fun!” Sam insisted for the fifth time.

You narrowed your eyes at Sam’s enthusiasm. “Since when are you so hoho-holidays?”

“I don’t know” he shrugged. “I guess I’ve never had a real Christmas before, except for the one before Dean went to hell. And I’ve never had a picture with Santa Claus either. I know its lame, but...”

“Wait, did you get the idea from when you were looking through my childhood photo albums last week?” you recalled, thinking back to a few days earlier when Sam found pictures of a three-year-old you on a mall Santa’s lap, smiling at the camera.

Sam’s face broke into a soft, dimpled smile, and he looked at the ground sheepishly. “Its been so long since the two of us have done something normal, so I figured, why not start with this?”

“A couple’s Santa portrait?” you asked wearily, feeling your resolve melt.

Sam shrugged again in response.

“Alright, fine,” you relented. “But if Santa turns out to be evil, its on you.”

Sam laughed and slung an arm over your shoulders as the two of you continued to wait for your turn.

A few minutes later, the child in front of you was being whisked away by his parents as he bawled, and a teenager dressed as an elf beckoned you and Sam forward.

“Just the two of you then?” the elf asked, uninterested.

“Yep,” Sam nodded. The elf strolled back to the camera without saying anything else, and then it was just you, Sam, and jolly old St. Nick himself.

Santa smiled broadly at you and Sam, or at least, you thought he did. It was hard to tell under the thick white beard. “Look at what we have here! Have the two of you been good this year?” he asked in a booming, peppy voice.

“Well I think Y/N’s been a little more naughty than nice, but I sure have,” Sam winked at you as the both of you took a seat on either side of Santa Claus. You blushed at what Sam was insinuating, and hoped that Santa hadn’t caught on to what Sam really meant.

Then the elf behind the camera got your attention, counted down from 3 to 1, and took the picture with a bright flash. When it was over and the elf handed you an envelope of your printed pictures, you and Sam thanked Santa and walked away so the next kid could get their turn. As you were existing the mall, you halted in you tracks, and pulled Sam to a stop as well.

“Woah wait...he didn’t give us candy canes!” you exclaimed. “They’re supposed to give out candy canes! What a rip off!”

Sam’s eyes grew wide, and his lips fought to contain a laugh. “I guess he really was Evil Santa after all.”


	12. Imagine you and Dean searching for your hidden presents

**Summary for the Chapter:**

> Reader x Dean - Fluff.

“The kitchen is all clear,” you told Dean over the phone while you tried to get the cupboards back in order. “You find anything in Sam’s room?”

“Yeah, a whole lot of nothing,” Dean’s voice scoffed through the speaker. “I turned the whole place upside down and found squat.”

“You are gonna clean it up before he gets home, right?”

“One step at a time, Y/N, we gotta find those presents first. Meet me back at the library when you’re done tidying up my kitchen,” Dean instructed before hanging up. You rolled your eyes at him, even though he was on the other side of the bunker. Of course he was more concerned with the mess in the kitchen than with the mess in his brother’s room.

Back at the library, Dean unrolled a hastily drawn blueprint of what appeared to be the bunker onto a table. “I figured we might need this after last year,” he said, prompting you to think back to how you and Dean had failed to find the presents the year prior because of a small hidden room that only Sam knew about.

“Since we agreed not to take on any cases for the entire week leading up to Christmas, I had the time to draw up this fine work of art.,” Dean beamed, proud of his accomplishment.

Without bothering to comment, you began to cross off the rooms that you had searched, and Dean did the same. Pretty soon, every single room on the map was marked.

“I don’t get it, its in his nature to buy us our gifts weeks ahead of time,” you commented once it became apparent that you and Dean had looked absolutely everywhere.

Dean pouted and groaned in frustration, “So where the hell is he hiding them?!”

Your eyes scanned the blueprint again, and something caught your attention. “Wait…did you check the cars, Dean?”

“Yep.”

“All of them?”

“Yeah Y/N, of course I checked all of them.”

“Including the Impala?”

Dean stared at you, his entire form perfectly still, as he processed what you were hinting at. “Son of a bitch!”

You and Dean had to wait another hour before Sam got home with the Impala before you could check it. As soon as the younger Winchester locked himself in his room, which Dean had finished cleaning only minutes before, you and Dean made a beeline for where it was parked in the garage. It didn’t take long before you found two wrapped boxes wedged under the front seat; one with your name and the other with Dean’s.

Dean laughed in triumph, and was about to open his present when you had second thoughts.

“Wait!” you stopped him. He shot you an annoyed look, which you chose to ignore. “Sam went through a lot of effort to wrap and hide these. Christmas is only a few days away. Can’t we at least make the effort to wait?”

Dean gazed longingly at the package in his hands, and shook his head a bit; as if he were having a back and forth conversation in his mind. “Fine,” he sighed after a few seconds. “You’re right, we should wait. But do we at least get bragging rights for winning this year?”

“Obviously,” you smirked right back at him.


	13. Imagine hunting a snow monster with Sam

**Summary for the Chapter:**

> Reader x Sam - Fluff & Angst.

“I can’t believe we’re hunting the Bumble!” you exclaimed, smacking Sam on the arm in your excitement.

Sam looked down at you as the both of you trudged through the snow, guns in hand. “It’s just a snow monster, Y/N, this isn’t a TV special.”

“ _Abominable_  snow monster,” you corrected. “And ‘Bumble’ is more fun to say. You think we’ll have to yank it’s teeth out to make it less murderous?”

“It kills with ice, not it’s teeth,” Sam said. “We could always try pushing it off a cliff, though.”

You loved the fact that he was playing along by referencing your favorite Christmas movie. “That won’t work,” you reminded him. “Bumbles bounce.”

Sam didn’t bother to argue with you. Instead, his lips tugged up into a grin and he bumped you playfully with his side as you continued to walk. You and Sam kept quiet for the rest of the journey to the part of the forest where the creature was rumored to be hiding out. After a while, it began to grow dark and the snow fell heavier and heavier, yet there was no sign of the monster.

“What is taking so long?” Sam hissed impatiently.

You shook your head and blew out a visible frosty breath. “No clue. It should have showed itself by now.”

“Maybe it’s busy terrorizing the North Pole,” Sam joked. You began to laugh, but the loud crack of a branch breaking disrupted the moment.

Instantly, you and Sam shifted into hunter mode.

Sam signaled for you to to circle the clearing on the left while he took the right, and then the two of you split up silently. You crept along the line of trees, squinting against the heavy downpour of snowflakes. Then a loud roar sounded somewhere off to your right, where Sam was supposed to be. You rushed towards him as fast as your could.

“What happened?” you asked Sam, who was alone and unharmed, when you got to him.

“I don’t know. It was coming right at me, and then something else got it’s attention and it disappeared,” he explained.

In a split second, Sam’s eyes widened as he fixed on something right over your shoulder. Before he could make a move, the air was forced from your lungs as the snow monster stabbed an icicle through your chest. You hardly felt any pain, only shock, which soon turned into sensation that burned cold close to your heart. 

Sam screamed your name and caught you before you could hit the ground. Then, with zero hesitation, he aimed his gun and unloaded the clip into the monster’s head, killing it.

When that was done, Sam held you close to your chest, engulfing your body with his own. He ran shaky fingers through your hair and examined your injury.

“Y/N...baby...stay with me okay? I’m gonna get you out of here. Just hold on,” Sam pleaded as lifted you from the ground and carried you away as fast as he could.

Through the haze of his words, all you could think about was how beautiful the scarlet of your blood looked against the stark white blanket of snow.


	14. Imagine Dean saving you from a disastrous family Christmas

**Summary for the Chapter:**

> Reader x Dean - Angst, fluff, romantic. This imagine is so short because it ended up turning into a full length one shot as I was writing it. Here's the full version - http://archiveofourown.org/works/5512319

**Notes for the Chapter:**

> WARNINGS: swearing, insults, verbal abuse from a parent.

You registered as your father’s arm reeled back, palm wide open, and you braced yourself for a slap that never came.

Instead, your father was jerked away from you and thrown against the opposite wall.

“DON’T YOU DARE TOUCH HER!” Dean roared in your father’s face. You had rarely ever seen Dean so angry. “Don’t you touch her, don’t you hit her, don’t even look at her.”

At this point, the rest of your family had gathered around to see what the commotion was about, but none of them were brave enough to intervene.

“Who the hell are you?” you father asked shakily, trying and failing to keep up a tough demeanor.

“I’m the man who loves your daughter, something you clearly don’t know how to do,” Dean snarled. “You make me sick. Y/N is the best person I’ve ever known. If you had any idea how amazing she is, you’d know that you have no right to even be near her.”

Your family members were all whispering among themselves, trying to figure out what the hell was going on, but you didn’t pay attention to them. You approached Dean and placed a hand on his arm. He turned his head to face you, and his green eyes softened as soon as they met yours.

“Dean, he’s not worth it. Let’s go,” you said gently. Dean watched you wearily, focusing on the wet streaks down your cheeks and the redness of your eyes, and then he looked back to your father. You knew what his protective instincts were telling him to do - to hurt your father so he could never hurt you again. But instead, Dean let him go and took your outstretched hand, following you to the door.


	15. Imagine Cas' reaction after watching "Its a Wonderful Life"

**Summary for the Chapter:**

> Reader x Cas - fluff & slight angst.

_Ding, ding, ding._

A high pitched ringing noise kept you on the brink of sleep. Grumbling to yourself, you begrudgingly got out of bed and followed the sound to it’s source. It wasn’t long before you stumbled upon a trench-coated man, standing before your Christmas tree; his finger flicking at the bell ornaments.

“Cas?” you asked hesitantly.

He turned around, startled, and stuffed his hands into his coat pockets. “”Y/N, did I wake you?”

“No, no, it’s alright,” you shook your head. “What are you doing?”

Cas remained quiet, refusing to meet you eye, but his expression spoke volumes. By his fidgeting and the way his jaw tightened, it was obvious to you that something was troubling him.

You took a few steps closer and spoke as gently as you could, “Castiel, tell me what’s wrong.”

He let out a deep sigh before speaking again. “ _It’s a Wonderful Life_.”

That wasn’t at all the answer you had expected. “Huh?”

“The movie watched earlier, _It’s a Wonderful Life_. The little girl said that an angel gets their wings every time a bell rings, so I thought…”

“You thought you’d try it out on yourself,” you finished for him. You realized, Cas wasn’t just troubled, he was _sad_.

“I know it was stupid,” he said quietly, sounding more like a lost child than a warrior for God.

You shook your head. “No, it’s not stupid at all.”

“I know it is impossible, for something as mundane as a bell to give wings to angels. I don’t know why I bothered.”

“Cas,” you pulled his hands out of his pockets and held onto them. “What you’ve been through, having your grace stolen from you and becoming human, it’s horrible. But you’re getting though it, magic bells or not.”

He smiled softly and squeezed your fingers. “Thank you, Y/N. I just wish I could be as good of an angel as Clarence was.”

“You’re so much better than Clarence,” you assured him.

“How do you know?” Cas asked, the sadness all but gone from his face.

“Because,” you told him, mirroring his smile. “You’re real.”


	16. Imagine staying up with Dean on the night before Christmas

**Summary for the Chapter:**

> Reader x Dean - Fluff.

**Notes for the Chapter:**

> It's 12:52 a.m. on December 25th (where I live), so...MERRY CHRISTMAS TO ONE AND ALL!!!

“How are you awake already?” Dean asked groggily, wiping the sleep from his eyes and glancing at the clock, which read 4:17 a.m.

“It’s Christmas, Dean!” you whispered with excitement, much like a young child. “I barely ever sleep on the night before Christmas, and then I’m always up super early to start the festivities anyways.” You bounced up and down in your spot, shaking the whole bed and rousing Dean into full consciousness.

“If this were a regular day, you’d be out cold and it would take a blow horn to wake you up,” Dean grumbled. 

“Well this isn’t a regular day,” you countered cheerily.

“Y’know, Y/N,” Dean said, sitting up to brace back against the headboard beside you, “Santa won’t come if you’re still awake.”

You chuckled a bit, and swatted his arm lightly. “I’m just excited, I can’t help it. I’ve always been this way.”

“Yeah?” Dean asked, never having experienced a Christmas sharing a bed with you before. “Tell me more.”

“Well,” you started, “Ever since I could remember, I’ve always been the first one up on Christmas morning. It’s a curse, honestly, because waiting for everyone else to wake up is pure _torture_ ,” you exaggerated your words, causing Dean to laugh and shake his head at you.

Dean stifled a yawn, and you were about to tell him to try to go back to sleep, but he slung an arm around your shoulders and said, “Go on.”

“Up until I was ten, I was always too scared to leave my room. So I had to wait for my parents to come get me and let me know that it was okay to go to the Christmas tree.”

“Wait, why were you scared?” Dean asked, genuinely invested in your story.

A blush rose to your cheeks. “I didn’t want to run into Santa, just in case he was still there when I woke up,” you admitted. “Ugh, I was so lame.”

Dean laughed lightly and kissed the side of your head. “Nah, you’re not lame. I was kinda scared of Santa Claus too. I mean, what kind of sick freak breaks into kids’ houses like that and eats their food?”

“Hey!” you exclaimed. “Don’t bad-mouth Santa. And besides, I wasn’t scared of him. I just didn’t want him to take me off the nice list.”

“Aww, young Y/N was adorable,” Dean fake gushed.

“Shut up,” you scoffed, unable to keep the smile from spreading on your lips.

Dean mussed your hair and smiled with you. “Grown up Y/N is adorable too.”

“You’re damn right I am,” you agreed. You shuffled closer to Dean and leaned into him, resting your head in the curve of his neck. “I’m probably not going to sleep at all for the rest of the night,” you told him, “but you should try and get some rest.”

Dean trailed his fingers up and down your spine, making you shiver despite the layers of clothes you had on. “No, I’m awake now. I’ll stay up with you.”

“Are you sure?”

“Yeah. You got me all excited for Christmas, too. I haven’t felt that in a very long time.” His eyes and smile were soft as he gazed down at you, and the fact that you were able to share your joy with him made you feel all warm and fuzzy inside.

_I guess this is what the holiday season is really about_ , you thought to yourself, just as Dean happily launched into the few Christmas stories from his own childhood.

**Notes for the Chapter:**

> The stories that Y/N told are all true btw. And yes, I'm still like that every year, haha. Whether or not you celebrate Christmas, I hope you have an amazing day :)


	17. Imagine giving Sam a real Christmas when he comes home from a hunt on December 25th

**Summary for the Chapter:**

> Reader x Sam - Fluff.

**Notes for the Chapter:**

> I know it’s after Christmas, but I still have a list of prompts to get through, so I’ll just keep writing them until they’re done. There’s one more Christmas-y prompt, and after that the rest will be winter/holiday themed.

“Y/N, we’re home!” Sam’s voice called out from the door, quickly followed by the sound of footsteps descending the stairs into the bunker.

You hastily placed the dishes onto the table and yelled, “Wait, don’t come in yet!” from the library.

“Come on Y/N, I gotta hit the head!” Dean complained loudly.

Holding back a snicker, you surveyed the room, making sure your work was perfect. Once you were satisfied, you called the boys in. Dean speed walked through the room first, only pausing to give you an impressed thumbs up, before he hurried off to the bathroom. Then Sam entered, staring straight at you with a soft smile on his lips. When he realized what you had done, he froze in place, eyes going wide.

Sam’s gaze swept over the decorations that adorned the room - the garlands, light, wreaths, and tinsel. He fixated on the tree you had put up, complete with wrapped presents underneath. Finally, he followed his nose to she course of a decadent scent - the feast you had prepared, spread out over a library table.

“Merry Christmas, Sam,” you said, waiting for him to react.

“Y/N,” he marveled, “this is…you’re amazing.” Sam took four steps to get to you, sweeping you up into his arms and twirling you around in a circle. Yours and his joyous laughter mingled together, echoing throughout the bunker.

When he set you back on your feet, keeping his arms around you, he leaned down and pressed a sweet kiss to your forehead. “I’m sorry I almost missed Christmas,” he murmured.

“Its okay.”

“And I’m sorry I didn’t get you a present.”

“I meant it when I told you not to.”

“How about this,” Sam paused, his dimples becoming prominent as he smiled shyly and held your hands to his chest. “My gift to you is my heart.”

Your breath hitched at his words. If it were any other scenario, you probably would have laughed at the cheesiness of the line, but the honesty in his eyes told you how much he truly meant it. And you realized that there was nothing you wanted more.

“That’s all I need,” you affirmed, pulling him down for a searing kiss.


	18. Imagine Dean discouraging you from driving to him in a snow storm

**Summary for the Chapter:**

> Reader x Dean - general.

**Notes for the Chapter:**

> **I know it's common sense, but please don't use your phones while driving, especially in a storm!** On a lighter note, we're FINALLY getting snow where I live! YAY!!!

“Now I’m begging you, for once, look out for yourself Y/N.”

“Dean, I’m only 30 minutes away. I can get you,” you insisted, hastily zipping up your coat with one hand and opening your car door with the other, all with your phone wedged between your cheek and shoulder. Not to mention your struggle to even get to your car in the massive blizzard that swirled around you.

“No Y/N, its too dangerous out there,” Dean’s voice hissed through the speaker.

You rolled your eyes, fully aware that he couldn’t see it. “Its not like you’re in a designated safe zone either.” You started the car and cranked the heat all the way up.

“Yeah well, I can handle myself.”

“You can handle yourself in a hospital that’s overrun with demons?” you asked him, pointing out the severity of his situation.

“Y/N…” Dean groaned, 

“Dean, shut up. I’m coming, end of story. Please, please don’t make a move until I get there.” You were driving now, with the phone’s speaker on as you tried to see and maneuver your way through the icy storm. 

“You’re too stubborn for your own good, did you know that?” Dean sighed in defeat, and you knew that he wouldn’t dare argue with you anymore.

“Yeah well,” you chuckled lightly, “I learned from the best.”

You could practically hear Dean’s prideful smirk over the phone. “Just be safe, okay?”

“You too,” you told him before you hung up and stepped on the gas pedal as hard as you possibly could.


End file.
